Development of a novel drug delivery system consisting of an antitumor agent tocopheryl succinate

Hama, Susumu; Utsumi, Satoru; Fukuda, Yuki; Nakayama, Kayoko; Okamura, Y; Tsuchiya, Hiroyuki; Fukuzawa, Kenji; Harashima, H.; Kogure, Kentaro

doi:10.1016/j.jconrel.2012.05.031

Cited by 35 publications

(51 citation statements)

References 46 publications

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“…The structures of the latter products were established on the basis of the analytical and spectral data. Thus, the 1 H-NMR spectrum of 7a showed the presence of δ 2.89 ppm assigned to the CH 3 group, a singlet at δ 4.89 ppm indicating the NH 2 group and a singlet at δ 8.33 ppm confirming the presence of the NH group. Moreover, the 13 C-NMR spectrum showed δ …”

Section: Introductionmentioning

confidence: 93%

“…Nowadays benzothiophene derivatives in combination with other ring systems have been used extensively in pharmaceutical applications. [1][2][3] A large number of compounds containing thiophene system have been investigated because of their broad spectrum of biological activities which include analgesic, 4 antibacterial, 5 antifungal, 6 antiparasitic, 7 antiviral, 8 anti-inflammatory, 9 anticonvulsant, 10 anti-nociceptive, 11 DNA cleavage, 12 herbicidal, 13 antitubercular, 14 protein kinase inhibition, 15 respiratory syndrome protease inactivation, 16 an active ester in the peptide synthesis and agonists of peroxisome proliferator activated receptors. 17 In addition to these considerable biological applications, tetrahydrobenzo [b]thiophenes are important intermediates, protecting groups and final products in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, cytotoxic and anti-proliferative activity of novel thiophene, thieno[2,3-b]pyridine and pyran derivatives derived from 4,5,6,7-tetrahydrobenzo[b]thiophene derivative

Mohareb

Abdo

Al-farouk

2017

ACSi

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Novel tetrahydrobenzo [b]thienopyrole derivatives are synthesized from 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene (1) through its reaction with α-chloroacetone to give the corresponding N-alkyl derivative 3. Compound 3 undergoes ready cyclization in sodium ethoxide solution to give the tetrahydrobenzo[b]thienopyrrole 4. The latter compound 4 is used as the key starting material for the synthesis of thiophene, thieno [2,3-b]pyridine and pyran derivatives. The cytotoxicity of the synthesized products towards the human cancer cell lines namely gastric cancer (NUGC), colon cancer (DLD-1), liver cancer (HA22T and HEPG-2), breast cancer (MCF-7), nasopharyngeal carcinoma (HONE-1) and normal fibroblast (WI-38) cell lines are measured. Compounds 4, 7a, 7b, 8a, 8b, 10c, 10d, 10f, 12a, 12b, 14b and 15b exhibit the optimal cytotoxic effect against cancer cell lines. Compounds 7b and 14b show the maximum inhibitory effect and these are much higher than the reference CHS-828 (pyridyl cyanoguanidine). On the other hand, the anti-proliferative evaluations of these compounds with high potency against the cancer cell lines L1210, Molt4/C8, CEM, K562, K562/4 and HCT116 show that compounds 7b and 8b give IC 50 's against Molt4/C8 and CEM cell lines higher than that of the reference, doxorubicin.

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Section: Introductionmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Synthesis, cytotoxic and anti-proliferative activity of novel thiophene, thieno[2,3-b]pyridine and pyran derivatives derived from 4,5,6,7-tetrahydrobenzo[b]thiophene derivative

Mohareb

Abdo

Al-farouk

2017

ACSi

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“…Moreover, TS-EPC-NVs taken up via the endocytotic pathway were effectively delivered to the cytosol. 40) Previously, it was reported that TS-induced apoptosis is triggered by interaction with mitochondrial or cytosolic proteins. 20,42) Thus, the enhanced anticancer activity of TS-EPC-NVs was suggested to be due to its efficient cytosolic delivery.…”

Section: Ts As a Novel Drug Carrier Materialsmentioning

confidence: 99%

“…40) Following the method in a previous report, 45) siRNA was condensed with a polycation, and then the polyplex was encapsulated into TS-EPC-NVs. As shown in Fig.…”

Section: Ts As a Novel Drug Carrier Materialsmentioning

confidence: 99%

Nanoparticles Consisting of Tocopheryl Succinate Are a Novel Drug-Delivery System with Multifaceted Antitumor Activity

Hama

Kogure

2014

Biological & Pharmaceutical Bulletin

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Tumor heterogeneity hampers the clinical efficacy of cancer chemotherapy. Therefore, it is necessary to develop a multifaceted, rational treatment strategy with the potential to modulate overall tumor heterogeneity. Since combination therapy using several drugs has been shown to have enhanced therapeutic effects compared with monotherapy, combining agents with different antitumor effects would be a multifaceted form of therapy to overcome tumor heterogeneity. Therefore, the development of effective drug-delivery system (DDS) carriers for combination therapy is required. The ideal DDS carrier for combination therapy should itself have antitumor activity in addition to the ability to deliver drugs to tumors. α-Tocopheryl succinate (TS), a succinic acid ester of α-tocopherol, has attracted attention as a unique antitumor agent, and TS itself can form nanoparticles. In this review, we introduce nanoparticles consisting of TS as a novel DDS carrier with multifaceted antitumor effects for combination therapy.

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“…Although the number of drugs is available in the market, the need of discovering the new anti-tumor drugs with better pharmacokinetic profile and lesser toxicity has become the main objective in the field of medicinal chemistry, and it is also due to the fast microbial resistance to the existing molecules [1]- [3]. A large number of…”

Section: Introductionmentioning

confidence: 99%

The Synthesis and Cytotoxicity of Novel Thiophene Derivatives Derived from 2-(4-Oxo-4,4-Dihydrothiazol-2-yl) Acetonitrile

Samir¹,

Hamed²

2016

IJOC

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The reaction of the 2-(4-oxo-4,4-dihydrothiazol-2-yl)acetonitrile 1 with cyaclopentanone (2) afforded the condensed product 3. The latter underwent a series of heterocyclizations through its reaction with different reagents. Moreover, compound 1 underwent the Gewald's thiophene to afford compounds 15 and 17. The reaction of either hydrazine hydrate or phenylhydrazine with compound 17 gave the hydrazide derivatives 19a and 19b, respectively. The cytotoxicity of the newly synthesized products was measured towards the three cancer cell lines MCF-7, NCI-H460 and SF-268. The study showed that compounds 3, 5, 9c, 11, 13a, 13c, 17 and 19b were the most active compounds towards the three cancer cell lines.

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Development of a novel drug delivery system consisting of an antitumor agent tocopheryl succinate

Cited by 35 publications

References 46 publications

Synthesis, cytotoxic and anti-proliferative activity of novel thiophene, thieno[2,3-b]pyridine and pyran derivatives derived from 4,5,6,7-tetrahydrobenzo[b]thiophene derivative

Synthesis, cytotoxic and anti-proliferative activity of novel thiophene, thieno[2,3-b]pyridine and pyran derivatives derived from 4,5,6,7-tetrahydrobenzo[b]thiophene derivative

Nanoparticles Consisting of Tocopheryl Succinate Are a Novel Drug-Delivery System with Multifaceted Antitumor Activity

The Synthesis and Cytotoxicity of Novel Thiophene Derivatives Derived from 2-(4-Oxo-4,4-Dihydrothiazol-2-yl) Acetonitrile

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